# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1178 data_nrb9804 _audit_creation_method 'manual editing of SHELXL template' _publ_contact_author_name 'Dr Neil R Branda' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_email Neil.Branda@ualberta.ca _publ_contact_author_fax '001 780 492 8231' _publ_contact_author_phone '001 780 492 8187' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data which is being submitted in support of an upcoming communication to be published in Chemical Communications (manuscript 8/08638I). Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; The self-assembly and spontaneous resolution of a hydrogen-bonded helix ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Norsten, Tyler B.' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'McDonald, Robert' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Branda, Neil R.' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _chemical_name_common 'di(2-pyrrolyl) thioketone' _chemical_formula_sum 'C9 H8 N2 S' _chemical_formula_weight 176.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.3510(2) _cell_length_b 13.8734(4) _cell_length_c 16.4273(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1675.31(8) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 44 _cell_measurement_theta_min 26.60 _cell_measurement_theta_max 29.33 _exptl_crystal_description prism _exptl_crystal_colour deep_red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method ? _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.927 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .1761 _exptl_absorpt_correction_T_max .3103 _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuKa _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 297 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2169 _diffrn_reflns_av_R_equivalents 0.1074 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.39 _diffrn_reflns_theta_max 57.42 _reflns_number_total 1113 _reflns_number_observed 1038 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0237P)^2^+0.2820P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1113 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_obs 0.0391 _refine_ls_wR_factor_all 0.1019 _refine_ls_wR_factor_obs 0.0990 _refine_ls_goodness_of_fit_all 1.155 _refine_ls_goodness_of_fit_obs 1.166 _refine_ls_restrained_S_all 1.155 _refine_ls_restrained_S_obs 1.166 _refine_ls_shift/esd_max -0.003 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S S 0.24827(6) 0.10572(4) 0.48545(5) 0.0489(3) Uani 1 d . . N1 N -0.1422(2) 0.14583(10) 0.43762(13) 0.0431(5) Uani 1 d . . H1 H -0.1012(2) 0.17101(10) 0.48253(13) 0.052 Uiso 1 calc R . N2 N 0.3754(2) -0.06710(12) 0.38823(12) 0.0465(5) Uani 1 d . . H2 H 0.4588(2) -0.03160(12) 0.41089(12) 0.056 Uiso 1 calc R . C1 C 0.1270(3) 0.04569(12) 0.41597(14) 0.0388(6) Uani 1 d . . C2 C -0.0506(2) 0.07918(13) 0.39151(14) 0.0387(5) Uani 1 d . . C3 C -0.1598(3) 0.06017(14) 0.3251(2) 0.0446(6) Uani 1 d . . H3 H -0.1326(3) 0.01777(14) 0.2822(2) 0.053 Uiso 1 calc R . C4 C -0.3182(3) 0.11515(14) 0.3331(2) 0.0502(7) Uani 1 d . . H4 H -0.4164(3) 0.11631(14) 0.2964(2) 0.060 Uiso 1 calc R . C5 C -0.3047(3) 0.16695(14) 0.4037(2) 0.0496(7) Uani 1 d . . H5 H -0.3924(3) 0.20947(14) 0.4247(2) 0.060 Uiso 1 calc R . C6 C 0.1948(2) -0.04183(13) 0.38040(15) 0.0399(5) Uani 1 d . . C7 C 0.1111(3) -0.11833(13) 0.3416(2) 0.0469(6) Uani 1 d . . H7 H -0.0130(3) -0.12249(13) 0.3283(2) 0.056 Uiso 1 calc R . C8 C 0.2425(3) -0.1882(2) 0.3258(2) 0.0583(8) Uani 1 d . . H8 H 0.2236(3) -0.2474(2) 0.2994(2) 0.070 Uiso 1 calc R . C9 C 0.4034(3) -0.15474(15) 0.3556(2) 0.0552(7) Uani 1 d . . H9 H 0.5153(3) -0.18746(15) 0.3538(2) 0.066 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0433(4) 0.0525(4) 0.0509(6) -0.0065(3) -0.0054(3) -0.0055(2) N1 0.0398(9) 0.0430(8) 0.0464(14) -0.0038(8) 0.0019(9) -0.0053(7) N2 0.0399(9) 0.0516(10) 0.0479(15) 0.0021(9) 0.0015(9) 0.0018(8) C1 0.0369(10) 0.0398(9) 0.040(2) 0.0065(10) 0.0031(10) -0.0076(7) C2 0.0377(10) 0.0371(9) 0.0414(15) 0.0022(9) 0.0021(10) -0.0057(8) C3 0.0465(11) 0.0467(10) 0.040(2) 0.0022(10) -0.0004(11) -0.0050(9) C4 0.0402(13) 0.0549(12) 0.055(2) 0.0070(11) -0.0058(12) -0.0049(9) C5 0.0375(11) 0.0462(10) 0.065(2) 0.0040(12) 0.0014(12) -0.0021(9) C6 0.0414(10) 0.0429(10) 0.0353(15) 0.0043(10) 0.0025(10) -0.0016(8) C7 0.0455(12) 0.0473(11) 0.048(2) -0.0002(10) 0.0008(12) -0.0013(9) C8 0.0693(15) 0.0453(12) 0.060(2) -0.0062(12) 0.0000(12) 0.0039(10) C9 0.0558(13) 0.0553(12) 0.054(2) 0.0017(12) 0.0040(13) 0.0137(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S C1 1.671(2) . ? N1 C5 1.351(3) . ? N1 C2 1.372(3) . ? N2 C9 1.344(3) . ? N2 C6 1.379(2) . ? C1 C6 1.437(3) . ? C1 C2 1.443(3) . ? C2 C3 1.380(3) . ? C3 C4 1.398(3) . ? C4 C5 1.368(4) . ? C6 C7 1.382(3) . ? C7 C8 1.393(3) . ? C8 C9 1.362(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 110.6(2) . . ? C9 N2 C6 109.9(2) . . ? C6 C1 C2 118.2(2) . . ? C6 C1 S 120.9(2) . . ? C2 C1 S 120.83(15) . . ? N1 C2 C3 106.3(2) . . ? N1 C2 C1 120.5(2) . . ? C3 C2 C1 133.2(2) . . ? C2 C3 C4 107.8(2) . . ? C5 C4 C3 107.8(2) . . ? N1 C5 C4 107.5(2) . . ? N2 C6 C7 106.0(2) . . ? N2 C6 C1 120.7(2) . . ? C7 C6 C1 133.0(2) . . ? C6 C7 C8 108.1(2) . . ? C9 C8 C7 107.4(2) . . ? N2 C9 C8 108.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 1.5(2) . . . . ? C5 N1 C2 C1 179.9(2) . . . . ? C6 C1 C2 N1 162.6(2) . . . . ? S C1 C2 N1 -16.0(3) . . . . ? C6 C1 C2 C3 -19.5(3) . . . . ? S C1 C2 C3 162.0(2) . . . . ? N1 C2 C3 C4 -0.9(2) . . . . ? C1 C2 C3 C4 -179.0(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C2 N1 C5 C4 -1.5(2) . . . . ? C3 C4 C5 N1 0.9(2) . . . . ? C9 N2 C6 C7 0.3(3) . . . . ? C9 N2 C6 C1 175.3(2) . . . . ? C2 C1 C6 N2 166.7(2) . . . . ? S C1 C6 N2 -14.7(3) . . . . ? C2 C1 C6 C7 -19.9(4) . . . . ? S C1 C6 C7 158.7(2) . . . . ? N2 C6 C7 C8 -0.7(3) . . . . ? C1 C6 C7 C8 -174.7(3) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C6 N2 C9 C8 0.2(3) . . . . ? C7 C8 C9 N2 -0.6(3) . . . . ? _refine_diff_density_max .187 _refine_diff_density_min -.250 _refine_diff_density_rms .072 data_nrb9809 _audit_creation_method 'manual editing of SHELXL template' _publ_contact_author_name 'Dr Neil R Branda' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_email Neil.Branda@ualberta.ca _publ_contact_author_fax '001 780 492 8231' _publ_contact_author_phone '001 780 492 8187' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data which is being submitted in support of an upcoming communication to be published in Chemical Communications (manuscript 8/08638I). Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; The self-assembly and spontaneous resolution of a hydrogen-bonded helix ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Norsten, Tyler B.' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'McDonald, Robert' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Branda, Neil R.' . ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _chemical_name_common 'di(2-pyrrolyl) ketone' _chemical_formula_sum 'C9 H8 N2 O' _chemical_formula_weight 160.17 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.9190(10) _cell_length_b 8.5690(10) _cell_length_c 14.9590(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 758.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method ? _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4159 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1678 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 41.13 _reflns_number_total 4159 _reflns_number_observed 1895 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.16(156) _refine_ls_number_reflns 4159 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1665 _refine_ls_R_factor_obs 0.0594 _refine_ls_wR_factor_all 0.1249 _refine_ls_wR_factor_obs 0.0995 _refine_ls_goodness_of_fit_all 0.894 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 0.894 _refine_ls_restrained_S_obs 1.067 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O O -0.1712(2) 0.31684(13) 0.08276(7) 0.0297(3) Uani 1 d . . N1 N 0.2331(2) 0.44802(14) 0.02733(8) 0.0241(3) Uani 1 d . . H1N H 0.2088(2) 0.35665(14) 0.00224(8) 0.029 Uiso 1 calc R . N2 N -0.4232(2) 0.4239(2) 0.22411(9) 0.0263(3) Uani 1 d . . H2N H -0.4966(2) 0.3571(2) 0.19011(9) 0.032 Uiso 1 calc R . C1 C -0.0971(2) 0.4319(2) 0.12482(10) 0.0211(3) Uani 1 d . . C2 C 0.1024(2) 0.5125(2) 0.09459(9) 0.0207(3) Uani 1 d . . C3 C 0.1980(2) 0.6566(2) 0.11449(10) 0.0238(3) Uani 1 d . . H3 H 0.1452(2) 0.7283(2) 0.15815(10) 0.029 Uiso 1 calc R . C4 C 0.3862(3) 0.6772(2) 0.05867(10) 0.0274(3) Uani 1 d . . H4 H 0.4838(3) 0.7652(2) 0.05744(10) 0.033 Uiso 1 calc R . C5 C 0.4027(3) 0.5458(2) 0.00596(10) 0.0273(4) Uani 1 d . . H5 H 0.5151(3) 0.5273(2) -0.03811(10) 0.033 Uiso 1 calc R . C6 C -0.2120(2) 0.4830(2) 0.20559(9) 0.0202(3) Uani 1 d . . C7 C -0.1568(2) 0.5814(2) 0.27635(10) 0.0228(3) Uani 1 d . . H7 H -0.0208(2) 0.6391(2) 0.28278(10) 0.027 Uiso 1 calc R . C8 C -0.3395(3) 0.5797(2) 0.33667(10) 0.0274(3) Uani 1 d . . H8 H -0.3490(3) 0.6353(2) 0.39147(10) 0.033 Uiso 1 calc R . C9 C -0.5014(3) 0.4825(2) 0.30142(11) 0.0282(4) Uani 1 d . . H9 H -0.6444(3) 0.4605(2) 0.32737(11) 0.034 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.0322(6) 0.0271(6) 0.0297(6) -0.0081(5) -0.0043(5) -0.0033(5) N1 0.0284(7) 0.0219(7) 0.0219(6) -0.0063(5) 0.0005(5) 0.0049(6) N2 0.0220(6) 0.0285(7) 0.0284(7) -0.0002(6) -0.0042(5) -0.0035(5) C1 0.0233(7) 0.0190(7) 0.0211(7) -0.0004(6) -0.0064(6) 0.0021(6) C2 0.0224(7) 0.0213(7) 0.0183(7) -0.0021(6) -0.0019(6) 0.0038(6) C3 0.0262(8) 0.0240(8) 0.0213(7) -0.0038(6) 0.0012(6) 0.0010(6) C4 0.0285(8) 0.0280(8) 0.0257(8) 0.0008(7) 0.0015(6) -0.0029(7) C5 0.0233(8) 0.0347(9) 0.0239(8) -0.0001(7) 0.0010(6) 0.0040(7) C6 0.0200(7) 0.0197(7) 0.0211(7) 0.0013(5) -0.0020(5) 0.0024(5) C7 0.0244(7) 0.0208(7) 0.0232(7) -0.0015(6) -0.0014(6) 0.0001(6) C8 0.0327(9) 0.0279(9) 0.0215(7) -0.0004(7) 0.0016(6) 0.0073(7) C9 0.0226(8) 0.0348(10) 0.0273(8) 0.0064(7) 0.0032(6) 0.0062(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O C1 1.249(2) . ? N1 C5 1.346(2) . ? N1 C2 1.384(2) . ? N2 C9 1.343(2) . ? N2 C6 1.377(2) . ? C1 C2 1.441(2) . ? C1 C6 1.454(2) . ? C2 C3 1.390(2) . ? C3 C4 1.403(2) . ? C4 C5 1.378(2) . ? C6 C7 1.392(2) . ? C7 C8 1.408(2) . ? C8 C9 1.375(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 109.93(12) . . ? C9 N2 C6 110.36(13) . . ? O C1 C2 120.52(14) . . ? O C1 C6 119.47(13) . . ? C2 C1 C6 120.00(13) . . ? N1 C2 C3 106.43(13) . . ? N1 C2 C1 119.66(13) . . ? C3 C2 C1 133.77(14) . . ? C2 C3 C4 107.91(14) . . ? C5 C4 C3 107.09(14) . . ? N1 C5 C4 108.64(14) . . ? N2 C6 C7 106.44(12) . . ? N2 C6 C1 118.73(13) . . ? C7 C6 C1 134.80(14) . . ? C6 C7 C8 107.53(13) . . ? C9 C8 C7 107.18(14) . . ? N2 C9 C8 108.47(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 0.2(2) . . . . ? C5 N1 C2 C1 176.52(13) . . . . ? O C1 C2 N1 -10.3(2) . . . . ? C6 C1 C2 N1 168.80(13) . . . . ? O C1 C2 C3 164.8(2) . . . . ? C6 C1 C2 C3 -16.1(2) . . . . ? N1 C2 C3 C4 0.0(2) . . . . ? C1 C2 C3 C4 -175.6(2) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C2 N1 C5 C4 -0.3(2) . . . . ? C3 C4 C5 N1 0.3(2) . . . . ? C9 N2 C6 C7 1.0(2) . . . . ? C9 N2 C6 C1 179.27(13) . . . . ? O C1 C6 N2 -12.7(2) . . . . ? C2 C1 C6 N2 168.16(12) . . . . ? O C1 C6 C7 165.0(2) . . . . ? C2 C1 C6 C7 -14.2(2) . . . . ? N2 C6 C7 C8 -0.3(2) . . . . ? C1 C6 C7 C8 -178.1(2) . . . . ? C6 C7 C8 C9 -0.5(2) . . . . ? C6 N2 C9 C8 -1.3(2) . . . . ? C7 C8 C9 N2 1.1(2) . . . . ? _refine_diff_density_max .256 _refine_diff_density_min -.322 _refine_diff_density_rms .061